Chloroform → HCID 67947007, compound

HRID 981293Notes

Reaction equation

HRID 981293 reaction equation
[BrH:1].C(O)(=O)C.C(OC([NH:16][CH:17]1[CH2:19][CH:18]1[C:20]1[C:21]([F:38])=[CH:22][C:23]2[C:33](=[O:34])[C:32]([C:35]([OH:37])=[O:36])=[CH:31][N:25]3[C@@H:26]([CH3:30])[CH2:27][O:28][C:29]=1[C:24]=23)=O)C1C=CC=CC=1.C(Cl)(Cl)Cl>O>[BrH:1].[NH2:16][CH:17]1[CH2:19][CH:18]1[C:20]1[C:21]([F:38])=[CH:22][C:23]2[C:33](=[O:34])[C:32]([C:35]([OH:37])=[O:36])=[CH:31][N:25]3[C@@H:26]([CH3:30])[CH2:27][O:28][C:29]=1[C:24]=23

Participants

5

Reactant 3

HCID 6212ChloroformHCID 18643558HCID 18643558, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 67947007HCID 67947007, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.5 ml of a 30% hydrogen bromide-acetic acid solution was added with ice-cooling, 50 mg of (S)-10-(2-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid. The resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. To the residue obtained were added 5 ml of chloroform and 5 ml of water in this order. The aqueous layer was separated. The solvent was removed by distillation under reduced pressure. Diethyl ether was added to the residue obtained and the resulting crystals were collected by filtration to obtain 30 mg (yield: 68.2%) of (S)-10-(2-aminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid hydrobromide.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customTo the residue obtained
  4. customThe aqueous layer was separated
  5. customThe solvent was removed by distillation under reduced pressure
  6. additionDiethyl ether was added to the residue
  7. customobtained
  8. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-68410b9d40844b3d9546304af603c4d4
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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